Bufadienolide derivatives, preparing process thereof, composition comprising the same and the use thereof

a technology of fadienolide and derivatives, applied in the field of pharmaceutical chemistry, can solve the problems of not meeting the phamaceutic activity of the above compounds, and achieve the effect of simple synthesizing route and easy preparation

Inactive Publication Date: 2013-01-03
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0086]The present invention designs and synthesizes a class of novel bufadienolide derivatives which have inhibitory activities against tumor cell lines and thus can be used a...

Problems solved by technology

However, the phamaceutic activities ...

Method used

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  • Bufadienolide derivatives, preparing process thereof, composition comprising the same and the use thereof
  • Bufadienolide derivatives, preparing process thereof, composition comprising the same and the use thereof
  • Bufadienolide derivatives, preparing process thereof, composition comprising the same and the use thereof

Examples

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example 1

Preparation of Compound II1B-01

[0089]

[0090]In a 50 mL round bottom flask, p-nitrophenyl chloroformate (1.206 g, 6 mmol) was dissolved in 10 mL of anhydrous dichloromethane, followed by addition of dry pyridine (0.67 mL). A white precipitate appeared immediately. A solution of bufalin (2 mmol) in dichloromethane (10 mL) was dropwisely added under nitrogen, and stirred at room temperature for 6 hours. After completion of the reaction, the reaction mixture was washed twice with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue passed through silica gel column chromatography (90:10, petroleum ether / acetone) to give an intermediate A.

[0091]In a 10 mL round bottom flask, the intermediate A was dissolved in 3 mL of dichloromethane, followed by addition of triethylamine (35 μL). N,N-dimethylethylenediamine (6 mmol) was added, and stirred at room temperature for 2 hours (hereinafter, the reaction time of similar reactions is determined by thin-l...

example 2

Preparation of Compound II1B-02

[0092]

[0093]The reaction operations were as the preparation of compound II1B-01, except that N,N-diethylethylenediamine was used instead of N,N-dimethylethylenediamine. The eluent for the silica gel column chromatography is petroleum ether / acetone / ammonia water (50:50:0.5), and the yield is 78%. 1H NMR (CDCl3, 300 MHz) δ: 7.84 (dd, 1H, J=9.6, 2.4 Hz), 7.22 (d, 1H, J=2.4 Hz), 6.25 (d, 1H, J=9.6 Hz), 5.21 (br s, 1H), 3.23 (d, 2H, J=5.4 Hz), 2.55 (m, 6H), 1.02 (t, 6H, J=7.2 Hz), 1.09-2.26 (m, 22H), 0.94 (s, 3H), 0.69 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ: 11.8, 11.8, 16.7, 21.5, 21.6, 23.9, 25.5, 26.6, 28.9, 29.9, 30.9, 32.9, 35.3, 36.0, 36.9, 38.7, 41.0, 42.5, 47.1, 47.1, 48.5, 51.4, 52.1, 70.7, 85.5, 115.4, 122.9, 147.1, 148.7, 156.6, 162.6; ESI-MS (m / z) 529.5 [M+1]+.

example 3

Preparation of Compound II1B-03

[0094]

[0095]The reaction operations were as the preparation of compound II1B-01, except that N,N,N′-trimethylethylenediamine was used instead of N,N-dimethylethylenediamine. The eluent for the silica gel column chromatography is petroleum ether / acetone / triethylamine (60:40:0.5), and the yield is 90%. 1H NMR (CDCl3, 300 MHz) δ: 7.83 (dd, 1H, J=9.6, 2.4 Hz), 7.22 (d, 1H, J=2.4 Hz), 6.24 (d, 1H, J=9.6 Hz), 4.99 (br s, 1H), 3.36 (t, 2H, J=7.2 Hz), 3.36 (s, 3H), 2.44 (t, 2H, J=7.2 Hz), 2.26 (s, 6H), 1.20-2.20 (m, 22H), 0.94 (s, 3H), 0.69 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ: 16.7, 21.5, 21.6, 24.1, 25.5, 26.6, 28.9, 29.8, 30.9, 32.9, 34.6, 35.3, 36.0, 37.4, 41.0, 42.5, 47.1, 45.9, 48.5, 51.4, 57.0, 57.4, 71.2, 85.4, 115.4, 122.9, 147.1, 148.7, 156.1, 162.6; ESI-MS (m / z) 515.3 [M+1]+.

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Abstract

The present invention provides a class of bufadienolide derivatives representing by the following formula I or pharmaceutically acceptable salts thereof, the preparing process thereof, pharmaceutical composition comprising the same and the use thereof. The bufadienolide derivatives have inhibitory activities against human-derived tumor cell lines, and thus can be used as a drug for treating malignancies.

Description

CROSS REFERENCE OF THE RELATED APPLICATION[0001]This application claims the benefits of the priorities of the Chinese invention patent application No. 201110180620.4 filed with SIPO of China on Jun. 30, 2011 and the Chinese Invention patent application No. 201210017717.8 filed with SIPO of China on Jan. 19, 2012, the disclosures of these applications are incorated herein by reference by their entirety, as totally described herein.FIELD OF THE INVENTION[0002]The present invention relates to the field of Pharmaceutical Chemistry, more specifically, to a class of bufadienolide derivatives, the preparing process thereof, pharmaceutical composition comprising the same and the use thereof. The bufadienolide derivatives have inhibitory activities against tumor cell lines, and thus can be used as a drug for treating malignancies.BACKGROUND OF THE INVENTION[0003]Tumor is one of the malignant diseases threatening the life of human. More than 5 millions peoples are dying of tumor every year al...

Claims

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Application Information

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IPC IPC(8): A61K31/585A61P35/02A61P35/00C07J41/00C07J43/00
CPCC07J43/003C07J41/0055A61P35/00A61P35/02
Inventor HU, LIHONGGUO, DEANXIAO, ZHIYONGLIU, XUANMA, BIAOLEI, MIN
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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